Réaction #302856

Équation de réaction

boron tribromide

compound 19

6-iodo-4′-methoxyflavone

→

compound 20

6-bromo-4′-hydroxyflavone

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températureunder cooling on ice
2. 2
   AutreAfter completion of the reaction
3. 3
   Autrepurified water (80 ml)
4. 4
   workup.ADDITIONwas added to the reaction solution
5. 5
   Extractionthe dichloromethane layer was extracted
6. 6
   SéchageThe extract was dried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

Mode opératoire

A dichloromethane solution (4.9 ml) that contained boron tribromide was slowly added to a dichloromethane solution (85 ml) that contained compound 19 (185 mg, 0.489 mmol) while stirring under cooling on ice, and the reaction was then carried out for 30 hours. After completion of the reaction, purified water (80 ml) was added to the reaction solution, and the dichloromethane layer was extracted. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate/hexane (1/4) as an elution solvent, so as to obtain a product of interest, 6-bromo-4′-hydroxyflavone (compound 20). Yield: 79 mg (yield constant: 44.3%) 1H NMR (300 MHz, DMSO6) 610.37 (s, 1H), 8.27 (s, 1H), 8.28-8.30 (m, 1H), 7.98 (d, J=8.4 Hz, 2H), 7.61 (d, J=8.7 Hz, 1H), 6.93-6.95 (m, 3H). MS m/z 364 (M+).

Source